Adipiplon

{{Short description|Chemical compound}}

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{{Distinguish|adipiodone}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 477242840

| IUPAC_name = 7-[(2-(3-fluoropyridin-2-yl)-1H-imidazol-1-yl)methyl]-2-methyl-8-propyl-[1,2,4]triazolo[1,5-c]pyrimidine

| image = Adipiplon.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number_Ref = {{cascite|changed|??}}

| CAS_number = 840486-93-3

| ATC_prefix = none

| ATC_suffix =

| PubChem =

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2103791

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 9373993

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = OPL214POJ1

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D08840

| C=18 | H=18 | F=1 | N=7

| smiles = n4c(C)nc1n4cnc(c1CCC)Cn2ccnc2-c3ncccc3F

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C18H18FN7/c1-3-5-13-15(22-11-26-17(13)23-12(2)24-26)10-25-9-8-21-18(25)16-14(19)6-4-7-20-16/h4,6-9,11H,3,5,10H2,1-2H3

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = UAMAIHOEGLEXSV-UHFFFAOYSA-N

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Adipiplon (developmental code name NG2-73) is an anxiolytic drug developed by Neurogen Corporation. It has similar effects to benzodiazepine drugs, but is structurally distinct and classed as a nonbenzodiazepine anxiolytic.

Adipiplon is a subtype-selective GABA_A receptor partial agonist, which binds preferentially to the α₃ subtype. This is significant as while several previous nonbenzodiazepine drugs have been developed that are selective for α_2/3 over the other subtypes, adipiplon is one of the first drugs selected for clinical development which can discriminate between α₂ and α₃, as well as showing a little affinity for the α₁ or α₅ subtypes — alpidem is selective for α₃ over α₂, but still has moderate affinity for α₁, whereas adipiplon is highly α₃-selective with little affinity for either α₁, α₂ or α₅.{{cite journal | vauthors = Vinkers CH, Olivier B, Hanania T, Min W, Schreiber R, Hopkins SC, Campbell U, Paterson N | title = Discriminative stimulus properties of GABAA receptor positive allosteric modulators TPA023, ocinaplon and NG2-73 in rats trained to discriminate chlordiazepoxide or zolpidem | journal = European Journal of Pharmacology | volume = 668 | issue = 1-2 | pages = 190–193 | date = October 2011 | pmid = 21762686 | doi = 10.1016/j.ejphar.2011.06.054 }}

Adipiplon was being researched as a potential medication for the treatment of anxiety and insomnia, and in 2008 it was being used in Phase IIb trials.{{cite web | url = http://www.neurogen.com/products/gaba%20insomnia.html | title = Pipeline Summary GABA: Adipiplon | work = Neurogen | archive-url = https://web.archive.org/web/20080411105736/http://www.neurogen.com/products/gaba%20insomnia.html | archive-date=April 11, 2008 }}{{cite web | url = https://www.drugs.com/clinical_trials/neurogen-announces-adipiplon-preclinical-clinical-data-presented-neuroscience-2007-2614.html | title = Neurogen Announces Adipiplon Preclinical and Clinical Data }}{{cite web | url = http://www.sleepreviewmag.com/sleep_report/2007-09-12_07.asp | title = Meet Adipiplon: The New Insomnia Drug | archive-url = https://web.archive.org/web/20080415004751/http://www.sleepreviewmag.com/sleep_report/2007-09-12_07.asp | archive-date=April 15, 2008 | work = Sleep Review }} These trials were suspended after significant next-day side effects were discovered.{{cite web | url = http://www.fiercebiotech.com/biotech/neurogen-announces-suspension-of-insomnia-study-adipiplon | title = Neurogen Announces Suspension of Insomnia Study with Adipiplon | work = Fierce Biotech | date = 14 July 2008}}